AI-Powered Invoicing, Accounting, and Payroll All in One Branded Workspace
Built for entrepreneurs, freelancers, contractors, family-owned shops, agencies, nonprofits, and growing teams alike — CheckSmith.ai™ brings branded invoicing, automated bookkeeping, payroll, client portals, and self-directed IRA tracking into one intelligent workspace. Bank-level security, transparent pricing, and AI that quietly handles the repetitive work so you always know exactly where your business stands and where it’s headed next.
How the AI Works
Invoicing and Accounting, Automated by AI
Spend less time on data entry and more time running your business. Our AI handles the repetitive financial work in the background.
Instant Invoice Capture
Upload or email any invoice. The AI extracts vendor, amount, due date, and line items so you can approve and send payments in seconds.
Auto-Categorized Books
Connected bank transactions are sorted into the right accounts automatically. Your ledger stays organized without manual tagging.
Smart Payroll Insights
The AI surfaces upcoming bills, late payments, and spending trends so you always know what your business can afford next.
Live Demo
Watch AI Read an Invoice and Post a Transaction
Pick a sample invoice and press play. In a few seconds you'll see CheckSmith.ai™ scan the document, extract every field, and draft a balanced journal entry — the same flow your team gets in the app.
Upload a PDF, PNG, JPG, or WEBP up to 6 MB. Your file is sent to the AI only for this preview — nothing is stored.
The Home Depot #4412
#HD-88213 · 2026-07-12
Press play to see extracted fields.
Waiting for extracted data…
Simulated preview using sample data. Sign in to run it on your own invoices.
Inside the Workspace
Real UI Examples of AI-Powered Financial Workflow
See how invoice drafts and categorized transactions look once the AI has done its work.
AI Invoice Draft
The AI extracts vendor, dates, line items, and suggests the right expense category before you approve.
Auto-Categorized Transactions
Connected bank feeds are sorted into accounts like Job Materials, Software, and Subcontractor Expense automatically.
Get Started in Minutes
What Happens After You Create Your Free Account?
No setup fees, no credit card, no confusion. Just four simple steps to financial clarity.
Create Your Free Account
Pick a workspace name and sign up in seconds — no credit card required.
Connect Your Accounts
Securely link your bank and business accounts for live payroll visibility.
Brand Your Workspace
Upload your logo and colors so every invoice looks like it came from you.
Send Your First Invoice
Or dive into accounting and self-directed IRA tracking right away.
Trusted by Independent Founders
From sign-up to first invoice sent
Owner-reported time back on accounting
So your books are always reachable
From onboarded SMB users this quarter
Built for Small and Mid-Sized Businesses
Owners Who Stopped Juggling Five Apps
Real feedback from founders and operators who moved their invoicing, books, and payroll tracking into a single branded workspace.
I stopped copying totals between three tools. Invoices go out branded, the deposits land in the ledger, and my accountant finally quit emailing me on Sundays.
The AI reads a receipt in seconds and drops it into the right account. What used to be a Friday-night ritual is a two-minute review on my phone now.
We connected our bank on a Tuesday and had clean books by Thursday. First platform that actually felt built for a 12-person crew, not a Fortune 500.
Why stitch together five apps when you can run your empire from one?
Smart Invoicing
Send professional, brand-aligned invoices in seconds. Automated follow-ups so you get paid faster.
Auto-Accounting
Categorize income and expenses with ease. Generate Profit & Loss reports on demand.
Self-Directed IRA
Track alternative retirement assets — real estate, private equity, and more — alongside your business.
Everything Included
A Complete Financial Toolkit
One workspace covers invoicing, books, retirement, branding, and the guardrails that keep it all safe.
Smart Invoicing
- Branded PDF invoices
- Line items, tax, and discounts
- Automatic overdue reminders
Automated Accounting
- Import or add entries
- Profit & Loss on demand
- Reconcile against bank feeds
Chart of Accounts
- Prebuilt industry templates
- Rename, add, or archive
- Mapped to standard reports
Self-Funded IRA
- Guided custodian setup
- Track alternative assets
- Contribution progress tracking
Custom Branding
- Per-workspace logo & colors
- Themed invoices and portals
- Client-facing brand preview
Team & Roles
- Owner, admin, accountant, member
- Scoped per workspace
- Audit log of admin actions
Bank-Level Security
- Row-level workspace isolation
- Short-lived signed sessions
- Regular security scans
AI Assistance
- Auto-categorize transactions
- Draft invoices from a prompt
- Plain-English books Q&A
CheckSmith.ai vs Wave vs QuickBooks
Everything Wave and QuickBooks Do, Plus a Retirement Engine
Match Wave's free basics and QuickBooks' pro-grade accounting — and add a self-directed IRA neither one offers.
- Branded Invoicing
- CheckSmith.ai
- Wave
- QuickBooks
- Recurring Invoices & Reminders
- CheckSmith.ai
- Wave
- QuickBooks
- Income & Expense Tracking
- CheckSmith.ai
- Wave
- QuickBooks
- Chart of Accounts & P&L Reports
- CheckSmith.ai
- Wave
- QuickBooks
- Bank & Credit Card Connections
- CheckSmith.ai
- Wave
- QuickBooks
- Multi-User Team Roles
- CheckSmith.ai
- Wave
- Limited
- QuickBooks
- Higher tiers
- Custom Branding Across the Entire Workspace
- CheckSmith.ai
- Wave
- Invoices only
- QuickBooks
- Invoices only
- AI Transaction Categorization & Q&A
- CheckSmith.ai
- Wave
- QuickBooks
- Categorization only
- Self-Directed IRA Setup (Partnered Custodian)CheckSmith.ai Exclusive
- CheckSmith.ai
- Wave
- QuickBooks
- Alternative Asset Tracking (Real Estate, PE, Metals)CheckSmith.ai Exclusive
- CheckSmith.ai
- Wave
- QuickBooks
- Retirement Contribution Progress & Custodian ExportsCheckSmith.ai Exclusive
- CheckSmith.ai
- Wave
- QuickBooks
- Retirement Performance Alongside Business BooksCheckSmith.ai Exclusive
- CheckSmith.ai
- Wave
- QuickBooks
| Capability | CheckSmith.ai | Wave | QuickBooks |
|---|---|---|---|
| Branded Invoicing | |||
| Recurring Invoices & Reminders | |||
| Income & Expense Tracking | |||
| Chart of Accounts & P&L Reports | |||
| Bank & Credit Card Connections | |||
| Multi-User Team Roles | Limited | Higher tiers | |
| Custom Branding Across the Entire Workspace | Invoices only | Invoices only | |
| AI Transaction Categorization & Q&A | Categorization only | ||
| Self-Directed IRA Setup (Partnered Custodian)CheckSmith.ai Exclusive | |||
| Alternative Asset Tracking (Real Estate, PE, Metals)CheckSmith.ai Exclusive | |||
| Retirement Contribution Progress & Custodian ExportsCheckSmith.ai Exclusive | |||
| Retirement Performance Alongside Business BooksCheckSmith.ai Exclusive |
Comparison based on publicly documented Wave and QuickBooks features as of 2026. Wave and QuickBooks are trademarks of their respective owners and are not affiliated with CheckSmith.ai.
Frequently Asked Questions
Quick Answers to Common Questions
Onboarding, custom branding, and self-funded IRA setup — explained simply.
Sign up, connect your bank and business accounts, and invite your team. Our guided setup walks you through invoicing, accounting, and IRA tracking in minutes — no accounting background required.
Yes. Upload your logo, choose brand colors, and apply them across invoices, client portals, reports, and email communications so every touchpoint feels like yours.
Open a self-directed IRA through our partnered custodian, link it to CheckSmith.ai™, and start tracking alternative assets like real estate, private equity, and precious metals alongside your business finances.
Absolutely. We use bank-level encryption, secure authentication, and role-based access controls. Your financial data is protected and never sold or shared without your permission.
Every plan includes email support and access to our knowledge base. Paid plans add priority chat support and dedicated onboarding assistance for you and your team.